Spiro-Annulation of Ene-diones with Iodonium Ylides: An Anomalous Cloke–Wilson Rearrangement for the Regioselective Synthesis of Spirodihydrobenzofurans
Abstract
An efficient synthesis of spirodihydrobenzofuran derivatives via the 1,4-conjugate addition of iodonium ylides to indene-1,3(2 H )-diones, followed by an anomalous Cloke–Wilson rearrangement is reported. This strategy demonstrates a broad substrate scope with a high degree of regioselectivity control. Computational studies involving the natural orbital bond analysis were explored to explain this anomalous formation of unconventional products. In case of alkyne-tethered indenediones, the same regioselectivity control was observed, but in the presence of scandium-triflate in dimethoxyethane (DME), the normal Cloke–Wilson product was observed as an exclusive product.
Fields of Study & Subjects
Cyclopropane Reaction Mechanisms
Catalytic Alkyne Reactions
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 11
- Pages
- 3950–3967
- Publication date
- 5 March 2026
- Language
- EN